Country singer David Nail performs at HGTV'S The Lodge At CMA Music Fest June 7, 2013 in Nashville, Tennessee.

Country singer David Nail performs at HGTV'S The Lodge At CMA Music Fest June 7, 2013 in Nashville, Tennessee. (Photo by Michael Loccisano/Getty Images for HGTV)

David Nail knows exactly how he would have handled success had it come as early in his career and as intense as it did for fellow country singer Taylor Swift, who was 16 when she released her debut album, which has sold over 5 million copies, and for whom Nail opened in 2011.

“Terribly,” Nail, 34, said without hesitation Monday over the phone.

Nail, who will perform Saturday at the inaugural Windy City Smokeout festival at Rush and Illinois streets, got a small glimpse of fame when he was signed to Mercury Nashville Records in his early 20s. His first single, “Memphis,” nearly made the Top 50 on the Billboard Hot Country Songs chart in 2002, but his self-titled debut was scrapped by the record company.

“I got carried away both personally and professionally,” Nail said. “It had a lot to do with being so young and not having true life experiences. I came from a small town and had never flown on a plane or seen the ocean, and was suddenly thrust into the lifestyle of nice hotels and nice meals. You think, ‘Wow, this is easy. The rest of my life is taken care of.’ But just as easy as it’s presented, it gets taken away.”

After parting ways with his label, Nail, who had scholarship offers to play college baseball, began helping his friend coach a traveling baseball team of all-stars. Nail credits those summers of teaching teenagers to achieve their dreams for pushing him to pursue his own aspirations.

Since returning to the music industry with his 2009 album “I’m About to Come Alive,” Nail, now signed with MCA Nashville, was nominated for a Best Male Vocal Country Performance Grammy for his song “Turning Home.” “Let It Rain” reached No. 1 on the Hot Country Songs chart.

“I think we live in an era where the fastest you can get from point A to point B is usually the best,” Nail said. “But for whatever reason, that’s never been the case with me. I think I’ve always taken a little longer than most. I know it sounds cliche, but having success take longer makes the view all the more sweeter when you get to the mountain top.”

While the hits have been nice, Nail said it’s respect that he truly values.

“Vince Gill told me, ‘It’s good to have a singer back on the radio,’ ” Nail said of the legendary country singer. “That was one of those moments where I wanted to call my dad and say, ‘You won’t believe what just happened.’ That’s something that’s very important to me, moving to town and getting respect. It took a long time for me to feel comfortable with my status in this town. To hear peers who I compete with for success acknowledge me, I just want to say, ‘Thank you so much.’ I’ve been trying to get that attention for years.”

Nail has made countless visits to Chicago over the years, either to perform or when he’s looking for an escape from Nashville, Tenn., and he’s befriended local athletes, including the Bears’ Jay Cutler and the White Sox’s Jake Peavy. Last month, Nail performed with Peavy at a benefit concert for the Jake Peavy Foundation.

Who has the better singing voice: Cutler or Peavy?

“I would definitely say Jake Peavy,” Nail said. “He’s talented, but he has some hesitancy, probably for the same reason I have hesitancy taking batting practice around professionals: He feels out of place.”

There have been times when Nail wonders what would have happened had he stuck with his own athletic career. He can’t help it, being the huge sports fan that he is.

“I’ve never lost interest in watching (baseball),” Nail said. “There were times later in life when I wondered, ‘What if I pursued it?’ But I always tell people I seemed to make the better business decision.”

Nail has a new song on the radio, “Whatever She’s Got,” and is expected to release his next album in 2014. Sure, he hasn’t reached Swift’s level of fame and success, but not many artists have.

“I’ve always admired how Taylor was able to keep her wits together at that age and stay out of trouble,” he said. “This may not feel like work, but it is work, and there’s more aspects to it than singing songs. I had to learn that the hard way. But I was lucky enough that I matured and that someone believed in me and was willing to take a chance on me.”